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415 MONROE STREET was an unremarkable building on an unremarkable street in the unremarkable town that is Hoboken, New Jersey. A four-story tenement surrounded by many of similar size and some much smaller, one and two story, the sort of buildings that defined the immigrant communities that grew up on both sides of New York’s Hudson River in the late nineteenth and early twentieth centuries. From the top of the building, located just twelve blocks from the shoreline, you could see the three churches of St. Ann, St. Francis, and Our Lady of Grace and St. Joseph, established in the area to cater to the optimistic Catholic emigrants who had streamed into the town hoping for a new life in America. Beyond these places of worship was the growing skyline of Manhattan, where some of the neighborhood’s residents traveled daily to try to make a living.

For many people, the American dream had come to a crashing halt in Hoboken, just five miles from where they had entered the United States at Ellis Island, the nation’s busiest immigration inspection station from around the turn of the nineteenth century. For Italian peasants from as far apart as the picturesque shores of Lake Como in northern Lombardy to the arid and tiny towns of Ragusa in southern Sicily, the hope of wealth and prosperity had given way to the harsh reality of life at the bottom of the immigrant ladder in the New World. At the time, German merchant classes occupied the top rung, a trend that would decline rapidly as a result of anti-German sentiment at the outbreak of World War I. Their dominance was followed by the Irish, who controlled the police and fire services, leaving the scraps for the Italians, many of whom arrived in the country without papers, prompting the denigrating nickname “WOP.”

Saverio Antonino Martino Sinatra was just twelve when he passed through the Ellis Island inspection in 1904 with his mother, Rosa, and his sisters, Angela and Dorotea. Francesco, his father, had traveled ahead and was already working in a pencil factory when his family arrived. Rosa appears not to have considered education essential to her son’s advancement, and Saverio, who had adopted the more Americanized moniker of “Marty,” remained illiterate. First apprenticed as a shoemaker, he turned in his late teens to prizefighting, adopting the pseudonym “Marty O’Brien,” possibly to ingratiate himself with the Irish locals but more likely because Italians were not allowed in the fight game. Marty had tattoos drawn all over his arms, but with a slight build and an asthmatic condition, he did not come across as fearsome or threatening, neither to his opponents nor to the local street gangs. He was also too laid back in personality to make any impact either in, or outside, the ring.

He had, however, made an impact on Natalie “Dolly” Garavente, another Italian immigrant who lived nearby. Dolly had left the town of Rossi in Liguria, northern Italy in the late 1800s and had settled with her family in Hoboken. Dolly and Marty had been seeing each other since late 1910, when she had just turned fifteen and he was eighteen, and Dolly would dress up in her brothers clothes, hair bunched up under his cap, to go to Marty’s bouts in a time when women were not allowed at boxing matches. Dolly’s brother, Dominick, was also a disguised Italian fighter and regular opponent of Marty’s.

The Ligurian Garaventes had little time for the Sicilian Sinatras and regarded the illiterate Marty as highly unsuitable for the daughter of a family keen on bettering itself. As a result, Dolly’s parents refused to countenance the relationship. When the Garaventes refused point blank to host a wedding, Dolly and Marty eloped. The most romantic destination within their means was Jersey City, four miles down the road, and it was there, in the city hall, on Valentine’s Day 1914, that they were married. The bridegroom’s occupation was registered as athlete, and the couple’s friends Anna Caruso and Harry Marrotta witnessed the ceremony. It was a tribute to Dolly’s courage to go down this path without her parents’ blessing and against the background of the importance of the act of marriage in the staunchly Catholic ethos of Italian culture, and all the more so among the immigrant community. It was also a vote of confidence in Marty who, although kind and decent in every respect, did not engender much confidence as a potential breadwinner. The couple would not starve though, because of the money Dolly’s mother made at her grocery store. But they had two great assets, the bond that had kept them together and Dolly’s ambition and maturity beyond her tender years.

When the dust from the secret wedding eventually settled, Dolly’s parents grudgingly accepted the union and the couple settled on Monroe Street. It was in a small, dark room of the tenement house, on December 12 of the following year, that the most life-changing event of the young couple’s lives was to occur. Dolly had become pregnant in the late spring, and as she began her labor the local midwife attended her, as was the custom in the community. Professional medical care was beyond the means of most, and with her sister and mother by her side, Dolly knew she would be delivering her baby with the most experience and attention at hand that she could hope for. After hours of labor, things seemed to stop abruptly, and Dolly was suddenly in great distress. This was most likely because at less than five feet in height, she had a small pelvic area, and the baby was so large that she couldn’t push any longer because of exhaustion. At once, everyone in the room became increasingly worried by the progress of the birth. Sensing danger and realizing that the solution was beyond her skills, the midwife called the local doctor. Ten minutes later he arrived, quickly recognized that this had to be a forceps procedure, and literally ripped the baby from the exhausted mother’s womb. The action, however crude, had been a matter of life and death. The doctor had not had time for niceties, knowing full well the potential consequence of two deaths as opposed to one. Safely delivering the child while making sure the mother survived was his priority in a time when infant mortality was extremely high.

A baby boy, weighing an enormous thirteen and a half pounds, was delivered with wounds to the left side of the head, including a scarred ear and a perforated eardrum. These would have a lifelong consequence for the baby, and the awful difficulty of the birth and its conclusion would ensure that Dolly would never give birth again. But nobody was inclined to blame the doctor, who after the delivery turned his medical attention to the mother and, in effect, played the role of lifesaver. The baby’s grandmother, concerned that the baby appeared lifeless, put him under a cold tap until he started to cry. In a time when most, if not all, births in deprived areas were at home and the chances of survival up to a year were less than fifty-fifty, the event was unremarkable for the denizens of this Italian ghetto, who were preparing to gather whatever meager means they could for Christmas. Generations later there would be more reason to remember it as the day that Francis Albert Sinatra entered this world.

From the start of their tenancy of the Monroe Street address, Dolly had cast her eyes on a better life, and the birth of Francis Albert provided a fresh impetus to her aspiration to leave the stench of poverty behind. As far as she was concerned, their tenancy of number 415 was to be as brief as possible, and no source of retrospective pride. She had her sights firmly set on the better side of the city, and that meant that she was not going to subscribe to the traditional role of stay-at-home mother. The money had to come in, and whatever that took she was prepared to do. This meant that for the foreseeable future her beloved son would be minded and brought up by the extended family. If the possible consequences of this for little Francis ever crossed Dolly’s mind, she stuck it in some mental drawer and threw away the key.

Hoboken was not the worst place to be if you lived on the right side or you took, or were given, decent opportunities, although being Italian was a definite minus in that regard. The Hoboken community had been formed as a township in 1849, and after a referendum six years later attained the status of a city. By the late part of the century, shipping lines were using it as a terminal port, and a railroad terminal was established on the waterfront. It was a bustling area with the busy Hudson River as its commercial focus. Hoboken was the major destination of the Hamburg line, the main carrier of immigrants from Germany to the United States, hence the large German population in the city and its environs. Shipbuilding and dry-dock activity had also become a major source of employment, as had some rapidly growing manufacturing enterprises and big companies such as Maxwell House and Lipton’s Tea. There was always work if you knew the right people, and Dolly set about acquiring some skills and cultivating connections, which, somewhat unusually for an Italian, were based among the Irish community.

Her first move in that direction came while she was recovering from the birth and planning little Frank’s baptism, which she would not attend. She bucked the long-established Italian tradition of choosing godparents from within the close family circle by asking Frank Garrick, an Irish friend of Marty’s, to be godfather. Garrick’s father, Thomas, happened to be a local police captain, and Dolly felt he could potentially do much more for her Frank than any Italian relative or friend. The godmother, Anna Gatto, was Italian though, and the ceremony took place in St. Francis Church on April 2, 1916, when Frank was four months old.

Dolly had been planning her next move. She knew how valued midwives were in the community, and how they always retained a strong residual loyalty from those whose babies they had brought into the world. So as soon as she was fit and able, Dolly elected to become one. Her informal training consisted of accompanying doctors who were called to home births until such time that she was able to do it on her own. A doctor was not within the budget of most of the Little Italy occupiers and other immigrant groupings all over the greater New York area, so the midwife became the principal assistance at birth. In time, Dolly would be seen running around the neighborhood carrying a little black bag and looking like a medical professional. The best of midwives were very good but, as Dolly’s personal experience had illustrated, often not good enough when complications arose in the process of giving birth.

If her newfound role was in some way inspired by the horror she endured when bringing her son into the world, her later “diversification” of her services would confirm Dolly’s ruthless drive to acquire the means to improve the family’s social status. That drive would not be interrupted by any moral considerations or religious constraints. Within a couple of years she had amended her midwife role, one which was charged with assisting the safe passage of the unborn, to assisting the very opposite. Dolly Sinatra became a backstreet abortionist and did so because destroying the unborn was more lucrative than saving it. The instruments of the abortionist were simple and crude; the modus operandi was to break the amniotic sac inside the womb with a sharp instrument. For Dolly, it was a long hatpin regarded as a fashion item of the time, giving her the nickname “Hatpin Dolly.”

For over half a century there had been a somewhat ambivalent attitude toward abortion. The church and most doctors opposed it and the press vilified it, but the law in general accommodated it, probably because rich and powerful society figures availed of the service to avoid shame or diminution of reputation. The most famous American abortionist was Mrs. Ann Lohman, aka Madame Restell, or Madame Killer, as she was better known. She operated a high-class abortion clinic in Manhattan but franchised her services to others including a woman in Hoboken by the name of Frederika Loss. This female abortionist and tavern owner who had a farm in the Hoboken and Weekhaven area had become a major player in one of the most famous and sensational unsolved murder cases in American criminal history. The case involved a beautiful young woman by the name of Mary Rogers, who worked in a famous Manhattan cigar shop owned by John Anderson. In July 1841 she sought, in some sense of desperation, a loan for an “emergency,” and her employer duly obliged without explanation of the nature of the emergency. On the weekend of July 25 she told her widowed mother, who ran a boarding house, and her fiancé, a boarder, that she was going to visit an aunt and other family. Three days later her battered body, with severe blunt trauma to the face, was fished from the Hudson River in Hoboken. The coroner found strange wounds in the area of the vagina. The beauty of the victim and the strange circumstances of the case created a media frenzy, and all sorts of theories arose to explain the case, not helped by a totally incompetent police investigation.

In November 1842, Frederika Loss came forward and gave a sworn statement that the death was a result of a failed abortion attempt, but she was ignored by the police despite the fact that items of the victim’s clothing had been found on the farm and that it was well known that the tavern served as an abortion location for Madame Restell’s operations. The crime remained unsolved, but the Police Gazette of February 21, 1846 produced an unequivocal attack on Madame Killer:

It is well known that females die in ordinary childbirth. How many then who enter her halls of death may be supposed to expire under her execrable butchery? An obscure hole in the earth; a consignment to the savage skill of the dissecting knife or a splash in the cold wave, with the scream of the night blast, for a requiem, is the only death service bestowed upon her victims. Witness this ye shores of Hudson. Witness this Hoboken beach!

Three decades later, there was still demand for abortion, and Hatpin Dolly was carrying on the long-established tradition in Hoboken. Despite the threat of prosecution if caught, she would have been very aware that her clients would, almost always, keep their silence and thereby make any legal action almost certain to fail. Dolly had by this time become something of a politician. She had a great ear for language and dialect and would get involved as a translator for her fellow Italian immigrants when they appeared before the courts. She also hooked up with the Democratic machine of New Jersey’s Hudson Company and acted as a conduit between Italians and city hall. Helping to deliver votes, and ensuring that favors were organized and returned, put her in an increasingly strong position in both the Italian and Irish communities, and her tenacious, organized approach to political clientelism ensured that she was very quickly becoming someone to be respected. She was rewarded for her unstinting work when she was appointed leader of the third ward in the ninth district, a position never before held by a woman. This was by no means a sinecure, as it was not a paid job, but Dolly knew full well that when the time came she would be able to reap whatever reward she might seek.

As Dolly expanded her business and developed her local connections, there was an unexpected boost for her fortunes when in April 1917 the United States entered the First World War. The first local consequence was the taking over of the Hamburg American line piers and the establishment of federal control over the port. The German domination of the commerce of Hoboken came to an abrupt end with martial law imposed on the area. Many of the local German families were summarily removed to Ellis Island while others simply left the city. The Irish now firmly occupied the top rung of the local immigrant ladder, and Dolly, with her connections, was poised to profit from her work on behalf of her political masters. The exit of her family to a better side of the city was moving closer to reality.

On October 7, 1914, the same year that Marty and Dolly had married, another couple had tied the knot two hundred miles away and in very different circumstances. Their antecedents, however, were not so far removed from the origins of the Sinatras. Another aspect that provided an echo to their situation was the resistance of the parents of the bride to the bridegroom. In terms of wealth and influence the marriage of Joseph P. Kennedy and Rose Fitzgerald united two of the most powerful Irish families in the Boston area. But their origins, in particular on the Kennedy side, could have been easily forgotten by the passage of time, as often happens when money and position conspire to obliterate the facts of the past. The history of all Irish immigrant families, at the time, was grounded in extreme poverty.

In 1849 Patrick Kennedy had left his family, who farmed twenty-five acres in Dunganstown, County Wexford, Ireland, and had made his way to Liverpool and boarded the Washington Irving bound for America and a better life. Onboard he met Bridget Murphy, also from Wexford and also fleeing the famine-torn land in which millions had perished. From the depths of despair and the specter of the unknown emerged not only hope but also love. Thus on the Atlantic, in the steerage of an ocean liner, was the foundation stone laid for a great American dynasty.

Having reached Boston, the couple married on September 26, 1849 and settled in the slum area in the east of the city, where dreadful living conditions and overcrowding facilitated the spread of disease, cholera in particular. In the lower depths of East Boston in shanties and dark, water-filled tenement basements, adults and children perished in droves. The area was known as a place where children were born to die. The average life expectancy of the Irish immigrant was five to six years after arrival. The tenement building on Liverpool Street where they settled was a three-story wooden house with an open stairway at the back, situated in a row of houses distinguished by a common backyard full of rubbish and open, stinking sewers. A public health commission from the time described the conditions for the inhabitants of such tenement buildings:

“Huddled together like brutes, without any regard to sex or age, or sense of decency; grown men and women sleeping together in the same apartment, and sometimes wife and husband, brothers and sisters in the same bed … self-respect, forethought, all high and noble virtues soon die out (and in their place) sullen indifference and despair or disorder, intemperance and utter degradation.”

Patrick Kennedy found work as a cooper and the couple had five children, three daughters and two sons, one of whom died in infancy from the dreaded cholera. The disease also made a widow of Bridget when Patrick succumbed to it, at just thirty-five, in 1858, the same year their last-born child, their remaining son, Patrick Joseph, was born. Bridget would prove more than able to overcome the premature death of her husband. The family moved to Border Street near the docks, where she somehow found the money to open a stationery and notions store, selling ribbons and sewing goods on the ground floor of the house, in time expanding it into a grocery and liquor store. Young Patrick, known as PJ, left school at fourteen and worked as a stevedore on the Boston docks. He saved as much money as he could and, later borrowing some from his mother, took over the ruin of a saloon on Haymarket Square and transformed it into the most popular drinking venue in East Boston. The venture moved him into wholesale and then importation of liquor.

Only in his mid-twenties, a handsome, solidly built young man with a mop of auburn hair and sporting the then-fashionable handlebar moustache, there was little doubt that he would escape his tenement origins. Loyalty to his fellow Irish immigrants made him unwilling, however, to desert the customers who had supported the creation of his good fortune. So, while of course minding the profits, he dispensed help and advice to some of the less-fortunate Irish immigrants who visited his premises. PJ was a young man of vision, and it quickly struck him that commercial success alone would not guarantee him influence and power in his area. He began to turn his sharp eye and considerable talent to politics.

In 1885 he ran as a representative of East Boston for the Massachusetts state legislature, was elected, and would go on to serve no fewer than five terms. In the interim his sisters had all married and his mother was happily running her own small business. In the twenty-seven years since the death of the family patriarch when the only surviving son was just over ten months old, the Kennedy family had thrived by the old-fashioned virtues of hard work, faith, and self-belief. PJ also knew that wealth alone would not move him up the class ladder. The upper echelons of Boston society of the time were tightly controlled by the “Brahmins,” descendants of old families, some of whom could trace their lineage back to the original English settlers of the northeastern United States.

In 1887 PJ married “upwardly.” His bride, Mary Augusta Hickey, was the daughter of a businessman and the sister of a police lieutenant. The Hickeys lived in a big mansion in Brockton and had all the trappings of wealth, including servants. After the marriage ceremony at the Church of the Holy Redeemer, the couple moved into an apartment on Meridian Street in the center of East Boston. A year later, their firstborn was named Joseph Patrick, and they would go on to have another boy, who died in infancy, and two daughters. Poignantly, and with an echo of her husband’s passing, Bridget died later the same year in December 1888, with the consolation, at least, of seeing the Kennedy name assured for the future. Young Joseph would continue where his grandmother and father had left off, but with a ruthless determination and single-mindedness which would, in time, make him one of the most significant Irish American political operators of the twentieth century.

In the North End of Boston, another Irish immigrant family had similar origins and ambitions as Joseph P. Kennedy. Thomas Fitzgerald had fled the Irish Famine in the company of an uncle and cousin on a ship bound for New York City. A huge storm had caused the vessel to be diverted to the alternative destination of Boston, and it was here that the Fitzgeralds had begun to put down roots. At the other end of the city from the Kennedys, the Fitzgeralds had experienced a parallel rise from poverty to prosperity in both business and politics.

In 1879, Thomas lost his wife, Rosanna, who was pregnant at the time, to a stroke. The couple had already lost two children in infancy and a young daughter to cholera, but there were no less than nine sons remaining. The most energetic and enterprising was John, and his father decided to send him to Boston Latin School and Harvard Medical School, but the boy had no interest in practicing medicine. Just six years later, when Thomas followed his wife to the grave, Johnny found himself in charge of the family. He began to amass property, involved himself in local politics with the Democrats, married Mary Josephine Hannon, and went on to have five children.

The firstborn daughter, Rose, arrived on July 22, 1890. As her other siblings, Eunice, Agnes, John F. Junior, and Thomas, duly arrived, her father concentrated less on family and more on politics. In 1894 he targeted a US congressional seat, running against Joseph O’ Neill, who was backed by some city bosses including PJ Kennedy. But the Wall Street panic of the previous year helped Fitzgerald over the line much to the irritation of PJ Kennedy. On the morning after his primary election victory, he shook hands with Kennedy, saying, “Now that the fight is over, PJ, let’s shake hands.” The handshake worked to Kennedy’s advantage, for the victorious congressman would ultimately put his considerable political machine behind the man who was once his rival. It was the forerunner of an alliance of far greater political significance, which neither of the men, with all their astuteness and vision, could ever have predicted.

“Honey Fitz,” as John Fitzgerald was now nicknamed, had a close affinity to his daughter Rose, and she would accompany him on long walks through his little empire, the North End. She first met Joe Kennedy when she was five and he seven on Old Orchard Beach in Maine, where the Fitzgeralds, Kennedys, and other up-and-coming Irish families spent time in the summer months. The next time they met was on the same beach when Rose was a sixteen-year-old, highly intelligent beauty and Joseph Patrick a lean, handsome young man of eighteen years with a fulsome head of dark hair, a charming personality, and a winning smile. There was obviously a strong attraction. Rose recalled later that Joe had “the most wonderful smile that lit up his entire face from within and made an instant impression on everyone he met.” Regardless of his close and protective relationship with his eldest daughter, Honey Fitz viewed any development of romance with a Kennedy with alarm. The Irish American community had made great progress in New England. From their mid-nineteenth-century position at the bottom of the social ladder, the immigrant Irish had risen dramatically, particularly in Boston. The Irish ran the fire and police departments, and in the mayor’s office, the surnames of the incumbent had changed from Brahmin names like Quincy and Lincoln to unmistakably Irish names like O’Brien and Collins. But there was a very definite pecking order, and the Kennedys, despite their newly found financial status, had insufficient influence for a union between Joe and the precious Rose to be a matter for consideration.

There is a very telling photograph of both family groups taken on the Old Orchard Beach in 1907. PJ Kennedy is second from the left with his characteristic handlebar moustache. Rose is next beside him in a long dress, flanked by her father, his fit frame in a bathing suit with a top. Second from the right is young Joe with his hair drawn back over what appears to be a defiant expression on his face. Rose is the only one in the frozen image with a shadow of a smile on her face. The photograph provides a portent of things to come.

The month after the photograph was taken, Joe went to Harvard while Rose travelled to Europe and then to a convent school in the Netherlands. In the normal order of Catholics in East Boston, boys would go to the colleges of the religion, Boston College or Holy Cross, but PJ and Mary, whose brother John had also attended, wanted the best for their son, and Boston Latin, the largely Protestant preserve of the Boston aristocrats, was chosen despite the constant exhortations of the city Cardinal for Catholics not to darken its august doors. PJ was a realist and knew full well that the Kennedy future would stagnate if confined to East Boston and the parochial politics of the Irish in the area. There were also the Boston Brahmins to contend with. Despite the progress of the Irish Americans, they still ruled the city beyond the Kennedy and Fitzgerald bailiwicks and had created an impregnable white Anglo-Saxon protestant empire. Knowing he and his family couldn’t beat the Brahmins, PJ’s logic was that they might have a better chance by joining them—so after school, Joe was sent to Harvard.

At Harvard, Joe performed indifferently in academic terms, and he never gained entry to the most prestigious clubs such as Porecellian, AD, or Fly. He just managed to be elected to a minor one, the Hasty Pudding. This would prove a bitter lesson in the club mentality of the ruling class of Boston, but one that would provide great motivation to better that class by any means available to him in his future business career.

One incident in his final year gave a firm indication of the modus operandi employed by the Kennedys when confronted with such obstacles. At Boston Latin he had excelled at baseball, making the school’s first team four years in a row and acting as captain for two. But while making the team in his final year in Harvard, he was not getting to play on the diamond at all. During the ninth inning in the final game of the year against Yale, with Harvard leading four to one, Chick McLaughlin, the pitcher and captain of their side, requested that Kennedy be brought on to play, which seemed to all a most unusual decision in the circumstances.

The Yale batter hit a sluggish return and was put out at first base by Kennedy. Kennedy’s move won the game for his team and gave Joe his varsity letter. When McLaughlin requested the winning ball Joe refused saying he had got the putout. So why had McLaughlin, someone clearly not enamored of Kennedy, brought Joe on in the first place? Sometime before the game a representative of PJ came to see the captain whom it was known would be looking for a movie theatre license after his graduation. He was made an offer he could not refuse. To get the license he would have to put Joe Kennedy in to play.

Graduating in 1912 with a BA in economics, Joe began to court Rose in a more serious fashion, later saying that he had no real interest in anyone else. His first job was as a state-employed bank examiner. A year later, the Columbia Trust Bank, in which his father had a significant stake, was the subject of a hostile takeover bid, and Joe borrowed $45,000 from family and friends and succeeded in beating off the predators. As a reward, the shareholders elected him as president of the bank, and at twenty-five years of age he boasted to the press that he was the youngest man in that position in the United States.

That may or may not have been true, but what reporter was going to trawl through a list of the banks in the most remote regions of the country to contradict the story? Joseph P. Kennedy had learned a lesson about the importance of manipulating the media to suit his own purposes. On this occasion he did it for two reasons: The first, no doubt, for career advancement. The second, to put Honey Fitz in his place and make a union with his daughter seem more attractive. The circulating rumors of a scandal involving Honey’s alleged dalliance with a cigarette girl must have weakened his moral imperative, because on October 7, 1914, Joseph P. Kennedy and Rose Elizabeth Fitzgerald were married and after a two-week honeymoon settled in a nice and growing Boston suburb by the name of Brookline, at the address of 83 Beals Street.

Their first child, Joseph Patrick, was born at the Kennedy summer home in Hull, Massachusetts, on July 28, 1915. He, in turn, was followed by John Fitzgerald Kennedy, born at the Beals Street residence on May 29, 1917, with the aid of the best medical care money could buy. The proud father already had plans in his mind for the advancement of his children, and he, like Dolly Sinatra, would ruthlessly and without any moral compass pursue his own dreams and make sure that those he didn’t achieve happened vicariously through his children.

WHILE DOLLY SINATRA was furthering her ambitions for her family, young Frank was looked after each day by his grandmother, Dolly’s mother, Rosa. When he began elementary school she collected him every day, obsessive about her grandson. Marty retired from his ignominious career in the ring after breaking both his wrists, but with no culture of men as child minders in those days, he would spend his days drinking coffee in various joints with men in a similar position of unemployment. To label Marty as a bum may be a little unfair, but it’s clear he had no ambition, was held back significantly by his illiteracy, and, with a forceful, go-getting wife, was happy to take a backseat.

To complicate domestic matters further, a cousin of Marty’s, Vincent Mazolla, had arrived from Italy and joined the household. A veteran of the First World War, he had sustained injuries, which left him with a limp and, possibly, a mild case of PTSD. All in all, he was a poor candidate for employment and therefore held in low regard by Dolly. For a while “Chit U,” as he was known, was given the housework Dolly didn’t have time to do. She had a superhuman appetite for work, but even she could not carry two adults as well as a child, and tapped her political masters to find the two some gainful employment and additional revenue for the household.

She found Chit U a job as a steward’s assistant on the docks. Next stop was the mayor’s office at city hall, where she informed an assistant that she wanted a job in the fire department for her husband. When she was told there was no vacancy, her reply was, “Make one.” Dolly’s attitude was simple: she never said no when asked to deliver votes, and she was not prepared to accept a negative when she needed delivery of a favor in return.

On August 1, 1926, Marty was appointed to the fire department, where he joined the predominantly Irish workforce on a salary of $2,000 per annum plus a pension. With three sets of wages coming in, and the addition of another role to her own portfolio—that of a weekend chocolate dipper in an ice cream parlor—after a tenancy of over a decade she was ready to think very seriously of abandoning the co-op in Monroe Street.

She found what she was looking for ten blocks away: a three-bedroom apartment at 703 Park Avenue for the not-inconsiderable-at-the-time sum of $65 a month. But it bought the respectability that Dolly craved, and the family moved there in September 1927. She was by now also compensating for being an absent mother by lavishing Frank with clothes and pocket money. He was shy and quiet by nature, but being the best-dressed kid in the neighborhood ensured that he got the attention that his character might not have attracted. Kids twelve years of age are naturally drawn to a contemporary whose pockets jingle, and Frank became popular among the boys from the Park Avenue Athletic Club as he shared his mother’s spoils with them and as she slipped them the occasional treat at the ice cream parlor. If Dolly’s parenting methods were coming up short, they simply reflected the theory and practice of her own life: everyone had their price, and most people could be bought. But the money was no substitute for love and attention, nor would it lessen the effects of the outbursts of her famous rage.

When that rage was focused on Frank she would beat him with a stick, on one occasion pushing him down the stairs, knocking him out. She alternated these displays of violent cruelty with hugs and kisses, which often followed directly after the beating. It left him in a constant state of confusion and alert, never knowing why or when she would turn on him. Dolly could have not chosen a better type of parental misbehavior to send a message of confusion to her only child. Her love was mixed with a liberal dose of hate, her generosity was tainted by cruelty, her attention was crossed with neglect, and it was all salted with desperately unpredictable emotive explosion, leaving psychological scars to match the physical ones he had received at birth. In later life, Frank would be prone to similar emotional explosions.

Love, in his experience, was already equated with an impermanent elation and hatred, the other side of the emotional coin forming an alliance with depression. And in his early adolescence, relentless spoiling further complicated this psychological maelstrom. The trouble was amplified by the fact that Frank was not like his father, the calm, almost laid-back Marty. He was, in temperament, anyway, the reflection of his mother. The adult Sinatra would later relate the emotional impact his mother had left on his younger self to Shirley McLaine: “She was a pisser. She scared the shit outta me. Never knew what she’d hate that I’d do.” He told Pete Hamill, the author of Why Sinatra Matters, “When I would get outta hand she would give me a rap with that little club; then she’d hug me to her breast.” It is well documented that the child who is a victim of such parental abuse can in later life turn full circle and become the abuser, and this is certainly true of Frank. And yet, to further confuse this tangled relationship, there is no doubt that without the help of Dolly, Frank Sinatra would have quickly faded into the shadows of anonymity and would never have gotten beyond the borders of Hoboken. Having assumed the singular role of carrying the family along her chosen path on her tiny but not frail shoulders, she was determined to see it through.

In June 1931 Frank graduated from junior high and lasted just two months as a student in A. J. Demarest High School. In the midst of the worst depression in the country’s history, he had abandoned his education, the one thing that might help him ride with the economic tide, whenever that came. The Great Depression, which was putting millions out of work across the country, doesn’t appear to have bitten too deeply in the Sinatra household, however. Dolly had just purchased a Lincoln convertible for $65 but didn’t need a hungry, unemployed mouth to feed, so in her usual fashion, she decided to chase down a favor.

It was not for nothing she had chosen Frank Garrick, by then the circulation manager of the Jersey Observer newspaper, to be her son’s godfather. Arriving at his office, she asked him for a job for Frank, and he was given one bundling newspapers on a delivery truck, a stark contrast to driving the convertible around Hoboken. Tiring quickly of this lowly occupation and believing that he was destined for greater things, Frank decided he wanted to be on the editorial staff as a sportswriter. But the manner in which he attempted to achieve this ambition was blatantly and ludicrously insensitive and showed the sense of entitlement that his mother had knocked into him.

A vacancy arose when a member of the sportswriting staff was killed in an automobile accident. Frank abandoned the delivery truck and sat in the office, in the seat previously occupied by the late-departed writer. Spotted by the editor who, understandably, inquired about his presence, he replied that Frank Garrick had appointed him to the position. When Frank was called and asked what had prompted the circulation manager to make an editorial appointment, the editor dispatched him to fire the disrespectful and insensitive employee. When Garrick imparted the bad news to Frank, he was met with a tirade of foul-mouthed abuse proving he was indeed his mother’s son, whose curses would bring a blush to the cheek of the most experienced of stevedores.

Garrick would recall many years later to Kitty Kelley in her 1986 biography His Way, the verbal abuse he was subjected by the spotty, skinny little teenager: “Oh the temper and the words and the filthy names he called me, like he was going to kill me. He called me every name in the book and then he stormed out.” Dolly never spoke to her son’s godfather again, which was entirely typical. The most innocuous of slights was sufficient to see someone permanently dismissed, persona non grata. That was Dolly, and it would become Frank.

Insofar as a career was concerned, Dolly wanted Frank to follow convention. In the immigrant world of northern New Jersey, decent employment meant factory work or, if you were Irish (or Italian if you had a wife like Dolly), a fireman or a policeman or a government worker. These positions were respectable, they were permanent with the protection of a strong union, and they were pensionable. By these criteria, being a singer did not constitute a job. By her own standards, education was not a prerequisite to gaining a profession as she had proved with midwifery, and Frank’s forty-seven days in the New Jersey High School system clearly took him out of the running for any employment that required any form of advanced education. The fact that this view fitted perfectly with a singing career escaped Dolly at the time, as did the huge rewards then available for those who achieved success.

The temptations and the incentives that a career in entertainment could bring had certainly not escaped her son. As he began to dabble in the singing world, he was keenly observing those beginning to carve out careers. At the top of the list was Bing Crosby, who had moved from performing with the Rhythm Boys to the Gus Arnheim Orchestra, and made his national radio debut with CBS, having signed with Brunswick Records in 1931. By 1932 he had appeared in his eighth movie, The Big Broadcast, a film in which he played himself, such was his notoriety. Crosby’s delivery was a soft, conversational tone, leading to the labeling of crooner-sentimental as a singing genre. While Crosby was the king, inspiring the young Sinatra to reflect the great crooner’s image by sticking a pipe in his mouth, Rudy Vallee and Russ Columbo also provided role models for the aspiring singer. So incensed was his mother with the idea of his following a professional singing career that Dolly completely lost the plot one evening upon seeing a picture of Crosby on Frank’s bedroom wall, throwing a shoe at it and screaming that he was only a bum.

From the outside it might have been hard to disagree with her. After all, the United States was in the midst of the Great Depression with large-scale unemployment, misery, and poverty. This teenage layabout, as she saw it, was fantasizing about singing and refusing to take on a job that might involve the minimum of drudgery. Her son wanted to be a star but was refusing to dirty his hands on the way. The irony was that, in his own way, he had an even greater sense of entitlement than Dolly. The urge to get Frank to take onboard the concept of employment was normal but was now amplified by the fact that at the end of 1931 the family had taken another step up the social ladder, having purchased a house at 841 Garden Street for the then-enormous sum of $13,400. Dolly’s view was that the least she might expect was a financial contribution from the youngest and, herself excepted, most-energetic member of the household.

Frank knew she would eventually capitulate, and she did, giving him money for sheet music, which he used to ingratiate himself with local musical combos, a favor that was returned by occasionally letting him onstage to sing a song. And she could see that he was hustling all the time to get a break, so she helped him by getting him into the Union Club on Hudson Street in Hoboken. Afterward, he did stints in Italian social clubs. It was small-fry stuff, but he had to start somewhere. The other, less-obvious work he did was to assiduously study the methods of the singers he admired, namely Crosby, Columbo, and Vallee, and the routes they had chosen to stardom. The map appeared to be fairly straightforward: get the singing spot with a band or orchestra, and do some touring and nightclub spots; exposure on radio was essential, and from there, to Hollywood. The key ingredient was talent, and, as the world would eventually discover, Frank had plenty of that. The skinny, young singer was doing the fieldwork and, in common with any such player, he needed a good bounce of the ball to get a break.

Given the financial disasters and general hardship caused by the depression, Sinatra’s timing might have been considered questionable. But, although he had no idea at the time, in fact it could not have been better, as critic and author John Lahr observed, “While record sales had collapsed to $5.5 million in the early years of the depression as the 1930s progressed they would rise and rise to $48.4 million at the end of the decade and by 1945 to $109 million. By 1938 half of all broadcast programs were recordings of, mostly live, popular music.”

In addition, between 1933 and 1939 the number of jukeboxes grew almost tenfold and, three years later, to close to half a million. There would be no quick fix; Frank would have to serve an apprenticeship, which was by his standards long, but, in reality, pretty short. As Lahr put it, “By the time he emerged from his apprenticeship as a dance band ballad singer with touring bands, the technology for success was all in place.” Dolly eventually came to realize that there was no point in resisting her son’s aspirations, so she subsidized his drive to break into a band by buying him portable speakers and a microphone.

Combined with the Lincoln convertible, Frank was suddenly a very attractive ally to any struggling band, and Dolly got him spots at roadhouses, nightclubs, and Democratic Party meetings. In 1934 there was an unexpected vacancy at the top table of crooners with the unexpected death of Russ Columbo, and while Frank was not then in a position to exploit the opportunity, he certainly would be later. In more than one way he had a closer affinity to Columbo than Bing Crosby. Like himself, Columbo was born to Italian immigrants in 1908, the twelfth child of a musician who then lived in Camden, New Jersey, about a hundred miles from Hoboken.

Like Sinatra he possessed both talent and drive and knew what he wanted from an early age. He left school at seventeen to travel the country with various bands in which he doubled on violin and vocals. He also played nightclubs and progressed to running one of his own. He had also starred in a few movies and would go on to have a relationship with the movie star Carole Lombard before being shot in a bizarre accident, at twenty-six, by the well-known celebrity photographer Lansing Brown. He was a classic example of the phrase “the beautiful and the damned.” While the young Sinatra could not have avoided taking in an event that matched the passing of Valentino, Columbo’s life and career probably spurred him on, as opposed to his wondering about the efficacy of pursuing a dream that might translate into a nightmare.

One way or another Frank was pursuing his journey. From pestering radio stations in New Jersey for appearance spots (without any immediate success) to pushing himself at every band that came his way, he was not behind when it came to putting himself forward. Local outfit The Three Flashes, made up of youngsters Jimmy Petrozelli, Patty Principe, and Freddy Tamburro, was just one of the groups Frank targeted.

Since 1922, regular entertainments were broadcast live, and in the later part of the decade the sponsored musical feature was the most popular program format, with the shows called after the name of the sponsor. As an indication of just how influential these shows were, in the same year that Sinatra was pushing himself, George Gershwin had been hosting his own program. It was vital for any aspiring entertainer to get on the airwaves, and the composer of the American classic “Rhapsody in Blue” was no exception. The programs at the time were almost always live because the inferior quality of phonographic discs discouraged the radio networks from making recorded programs. As a result, prime-time shows would be performed twice, once for each coast of the country. For fame, wide reach, and promotion of the orchestra, band, and individual artist, radio was the biggest game in town.

The biggest radio act of the time was the talent show. As if to demonstrate the obvious that there is nothing truly new in any era, including the entertainment business, Major Bowes Original Amateur Hour was the America’s Got Talent